Chatham, MA Homes for Sale

Beautiful and Historic Chatham, MA

Chatham, located on the southeastern tip of Cape Cod, is known for its beautiful beaches, charming downtown area, and rich maritime history. The town is a popular destination for tourists and second homeowners alike, drawn to its picturesque landscapes and peaceful atmosphere. With a variety of housing options, from quaint cottages to luxurious waterfront estates, there is something for everyone in Chatham.

Real Estate Market Overview

The real estate market in Chatham is strong, with a mix of year-round residents and seasonal visitors driving demand for properties. Prices have steadily increased in recent years, reflecting the town's desirability and limited inventory. Waterfront homes command the highest prices, while properties further inland offer more affordable options for those looking to buy in Chatham. With the market being competitive, it is important for buyers to act quickly and decisively when properties become available.

Chatham's Neighborhoods

Chatham is home to several distinct neighborhoods, each with its own unique charm and character. The downtown area is a hub of activity, with shops, restaurants, and galleries lining Main Street. The Old Village neighborhood is known for its historic homes and scenic views of the harbor. North Chatham boasts spacious properties with water access, while South Chatham offers a mix of year-round and vacation homes near the ocean. Buyers in Chatham have a variety of neighborhoods to choose from, each offering its own appeal.

Investing in Chatham Real Estate

With its prime location on Cape Cod and strong market fundamentals, investing in real estate in Chatham can be a sound financial decision. Rental properties are in high demand, providing a steady income stream for investors. Vacation homes can also be a smart investment, with the potential for rental income and appreciation over time. Whether you are looking for a second home, a rental property, or a permanent residence, Chatham offers a range of opportunities for real estate investors.

Working with a Local Real Estate Agent

When buying or selling a home in Chatham, it is essential to work with a knowledgeable local real estate agent who understands the intricacies of the market. A local agent can help you navigate the buying or selling process, provide valuable insights into pricing and market trends, and connect you with the right properties or buyers. With their expertise and connections, a local real estate agent can streamline the real estate transaction and help you achieve your goals in the Chatham market.

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Newest Chatham, MA Homes for Sale

$2,195,000

3 Beds ⋅ 4 Baths ⋅ 73289843 MLS

South of 28 and situated on a quiet sandy lane in West Chatham, this home is the perfect beach house just a short distance to both Barn Hill Landing and Hardings Beach. Recently renovated, the home exudes coastal style living and offers superbly designed indoor and outdoor spaces. The house welcomes with an open concept great room with cathedral ceilings, abundant light and a fireplace with shiplap finish work. The modern kitchen is open and airy with quartzite counters, floating wood shelves and a large island that adjoins a dining area. The sunny family room with double french doors to a deck offers comfort & privacy in the back. The main level is complete with a bedroom, full bath with laundry and an attached 1 car garage. Above is a generous sized master suite with a walk-in closet and expansive full bathroom as well as a roomy bunk room complemented by a full bath. The lower level is fully finished.

53 Ocean Port Ln, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$1,900,000

4 Beds ⋅ 2 Baths ⋅ 73283473 MLS

Coming Soon when rentals finish.WOW! A RARE opportunity in the Village to own this charming quintessential 3 Bedroom/1 Bath bungalow plus detached 2 car garage with apartment over that includes living/dining/kitchen/sunny deck &1 Bed/1 bath. The main house 1st FL welcomes you with a sun porch entrance, open living/dining & cozy kitchen, a large covered deck at rear & sunny side deck, 2bed/1bath, stack W/D. The 2nd FL offers you the 3rd bedroom with unfinished attic for more potential. Property has a right of way over 40 Hallet Lane driveway for access to the 2nd unit in rear &more parking area which is a big plus! This well maintained older home is sold AS IS, offering a buyer to improve as they wish. Seller improvements:Title V septic system for 4 bedrooms, newer roof, gas heat, mini split in apartment and more. First showings, OPEN HOUSE, Sat. Sept. 14th, 12-2PM and Sunday Sept. 15th 12-2PM. All offers submitted by Wed. Sept.18th 5PM.Old Village National Register District.

67 School St, Chatham

Listing courtesy of Listing Agent: The Nickerson Power Group from Listing Office: Kinlin Grover Compass.

$995,000

4 Beds ⋅ 2 Baths ⋅ 73289289 MLS

This is a great opportunity and value to own a cottage in the Hardings Beach area. Walking distance to Barn Hill Landing and 1.3 miles to Hardings Beach, this cottage sits on an elevated parcel with mature plantings and a fenced-in backyard creating a peaceful retreat. The main floor opens to a living room with fireplace adjoined by kitchen with laundry and dining room that opens to a backyard patio. There are two bedrooms and a full bath on the first floor and two bedrooms and a shared bath above. There is also a full basement for ample storage. This close to beach location offers an opportunity to make it your own Chatham beach cottage.

56 Chatfield Ln, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$2,999,999

4 Beds ⋅ 4 Baths ⋅ 73286833 MLS

Rare opportunity in Mattaquason Point Association! This 4-bedroom 4-bath home is being offered for the first time in a generation. Sited on almost half an acre, and steps away from both downtown Chatham and Lighthouse Beach, this private neighborhood also boasts deeded access to ''the sandbox'' on Chatham Harbor where you can enjoy the morning sunrise on association-owned Adirondack chairs... or stay home and watch it from your very own widow's walk! Chatham Bars Inn and Andrew Hardings Beach are also just a short stroll away. With 2400 square feet of living space and a sprawling yard, this home is perfect for entertaining guests and extended family. Each of the 4 bedrooms has access to its own full bath, including a very private master with its own east-facing balcony; and the large kitchen, dining area and living room will make everyone feel right at home. Leave the keys at home and forget about the car as you enjoy shopping, dining, golf, and several different beaches from this in-t

47 Quasson Rd, Chatham

Listing courtesy of Listing Agent: Kristin Muller from Listing Office: John C. Ricotta & Associates, Inc..

$1,377,000

5 Beds ⋅ 10 Baths ⋅ 73288725 MLS

New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed by Pacaso. Set on 2.74 acres, Fox Hill offers a private sanctuary with 11,000 square feet of sophisticated coastal luxury. The renovated retreat has stunning views of Crows Pond, Eastward Ho and Pleasant Bay, and a private boat dock. The open, airy living room has a stone fireplace and window seats, and offers vast water views. More views are served up in the chef's kitchen, which features a Wolf gas range, a large island with seating, and doors to an expansive deck overlooking Crows Pond. A cased opening from the kitchen leads to the formal dining room with traditional raised panel walls and a butler's pantry with a wet bar. The three-level home includes a quiet office area for work, a lower-level gym for working out, and an outdoor pool and indoor sauna for pure relaxation. An elevator makes it easy to move between floors. The home, close to Lighthouse Beach, comes fully furnished and decorated.

558 Fox Hill Rd, Chatham

Listing courtesy of Listing Agent: John DePreaux from Listing Office: Corcoran Property Advisors.

$5,000

4 Beds ⋅ 2 Baths ⋅ 73288458 MLS

Available furnished rental November 1- April 30! Relax with the whole family at this peaceful place to stay. A stunning, fresh, contemporary home in Chatham! Perched upon a gentle hill at the very end of a cul-de-sac in Riverbay Estates, this home has undergone a total makeover. Airy and open, with soaring ceilings, designer Tala lights and a dramatic limestone gas fireplace that accentuate the kitchen/living room combo, AC, outdoor grill. Embrace the impending magic of another Cape Cod summer! Pets are allowed with specific approval only. Fireplace isn't for tenant use. A perfect rental for wedding parties : a 2 minute drive to Wequassett Resort, a 7 minute drive to Chatham Bars Inn, downtown Chatham and Lighthouse beach, a 3 minute drive to Jackknife beach.

101A Monomoyic Way, Chatham

Listing courtesy of Listing Agent: Steven Cohen Team from Listing Office: Keller Williams Realty Boston-Metro | Back Bay.

$999,999

3 Beds ⋅ 2 Baths ⋅ 73287739 MLS

Situated in a highly desirable, private enclave, 62 Duck Marsh Lane embodies the charm and allure of Cape Cod living with a convenient location within Chatham. Its prime location offers easy access to North Chatham, as well as Chatham's famous Main Street and beaches, plus the vibrant Orleans and Harwich hot spots.With authentic cedar shingle siding and beautifully manicured landscaping, this home exudes classic Cape Cod charm. Sunlight pours into the spacious interior through an abundance of windows, highlighting the high ceilings in the great room, perfect for entertaining. The renovated kitchen, a chef's dream, is the heart of the home, designed for gathering and enjoyment. An expansive deck off the back beckons for family gatherings and summer fun.Set on a desirable corner lot just shy of half an acre, this move-in-ready property has been tastefully updated throughout. Whether you're planting roots, seeking a seasonal retreat, this is a must see home.

62 Duck Marsh, Chatham

Listing courtesy of Listing Agent: Tony Guthrie from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

$2,995

2 Beds ⋅ 1 Baths ⋅ 73285033 MLS

Off Season Rental! Available 11/1 - 4/30 only! Welcome to this charming furnished 2 Bed 1 Bath Ranch, a true Chatham gem that has undergone a complete renovation, offering modern comforts and stylish finishes throughout. The open-concept layout features a fully equipped kitchen with stainless steel appliances and inviting island providing ample space for preparation and entertaining. The kitchen flows into the spacious living and dining areas. The bathroom has been tastefully updated and includes new laundry machines for an added convenience. This home boasts two generously sized bedrooms, one with a king size bed and the other with two queens. Other amenities include an EV charger and back yard oasis with a large deck, fenced in yard, and outdoor shower. Perfectly situated only 1.3 miles from Ridgeval beach, .5 miles to Schoolhouse Pond, and close to parks, shopping and restaurants.

175 Sam Ryder Rd, Chatham

Listing courtesy of Listing Agent: Alison Shanley Kennedy from Listing Office: Keller Williams Realty Signature Properties.

$1,790,000

3 Beds ⋅ 2 Baths ⋅ 73284799 MLS

Located on a tranquil private lane in highly desirable North Chatham, 17 Menekish Lane is on the market for the first time. A scenic stroll or bike ride of less than a mile takes you to the heart of charming downtown Chatham, where boutique shops, delightful restaurants, and the iconic Chatham Bars Inn await. The stunning beaches of Chatham are also just minutes away, offering the quintessential Cape Cod experience.Thoughtfully designed with classic post and beam architecture, this custom home features exposed wood beams, and a floor to ceiling wood burning fireplace, setting the stage for many enjoyable friends and family gatherings. And a must-see, soaring cathedral ceiling in the living room provides a unique blend of timeless character and charm. Whether you’re looking for a seasonal retreat or a year-round residence, its prime location and endless potential makes this one-of-a-kind home a rare find in North Chatham.

17 Menekish Ln, Chatham

Listing courtesy of Listing Agent: Daren Marvin from Listing Office: Sotheby's International Realty.

$1,475,000

4 Beds ⋅ 2 Baths ⋅ 73283813 MLS

Experience the pinnacle of Cape Cod living in this charming home located in the exclusive Harbor Cove Association. This coastal property offers a rare combination of privacy, style, and access to some of the most coveted waters in town. Just a leisurely 5-minute stroll from your doorstep lies the private association beach on Crow's Pond, where you can enjoy serene water views, sunbathing, or kayaking. Boating enthusiasts will delight in the availability to the mooring field providing deep water access to Bassing Harbor, Ryder's Cove, Pleasant Bay and beyond. Step inside to a world of refined comfort, with an open-concept living space filled with elegance, style, and an abundance of natural light. The bright and airy 4-season sunroom is an ideal spot to relax with a morning coffee while enjoying privacy and views of the lush surroundings. Outside, the expansive Azek decking provides the perfect setting for entertaining guests or enjoying quiet evenings under the stars. Grab this Gem!

121 Middle Rd, Chatham

Listing courtesy of Listing Agent: Sharon Mabile from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

$4,250

3 Beds ⋅ 2 Baths ⋅ 73283636 MLS

This stunning direct waterfront property offers 1916 sf of living space and sits on a quiet dead end street! As you step inside,you'll be greeted by tranquil privacy creating an atmosphere of elegance and luxury.The eat-in kitchen is perfect for summer lobstah bakes or fire up that grill on warm summer evenings.If you're feeling adventurous,take advantage of the pond access,where you can swim,fish, canoe! 3 Bedrooms include first floor master! Two full baths (two batubs) Large eat in kitchen with room for 6 barstools! Huge deck overlooking Mill Pond. Oversized living room.

35 Duncan Ln, Chatham

Listing courtesy of Listing Agent: Lauren Habeeb from Listing Office: Alliance Realty Advisors, Inc..

$1,951,929

4 Beds ⋅ 3 Baths ⋅ 73283515 MLS

A bright and airy sunlit home with open floor plan, is inviting family and guests to gather around the 8' breakfast bar making wonderful memories together. Enjoy the serenity of the 3-season screened room off the kitchen. The primary bedroom has a huge walk in closet and large private bath with granite countertops, tiled shower and floors. The home office is on the first floor and the laundry room boasts almost new appliances. This home has many closets and pantry area so no worries about storage. The closets are even well made with wooden shelving. Irrigation is on a private well and there is room for a pool. 'Seller welcomes offers with requests for buyer concessions.

1 Williams Way, Chatham

Listing courtesy of Listing Agent: Darci Sequin from Listing Office: Gibson Sotheby's International Realty.

$1,150,000

3 Beds ⋅ 2 Baths ⋅ 73283417 MLS

35 Duncan Ln, Chatham

Listing courtesy of Listing Agent: Lauren Habeeb from Listing Office: Alliance Realty Advisors, Inc..

$8,500,000

4 Beds ⋅ 5 Baths ⋅ 73283329 MLS

Spectacular waterfront home in a highly desirable location with stellar views of Bassing Harbor and the Atlantic. High end construction and easy one floor living with an open floor plan and primary bedroom on the first floor, office over the garage, and guest bedrooms upstairs. Lower level provides additional living space with full windows and doors and water views rivaling the rest of the house. Built in 2012 and meticulously maintained so it feels brand new. Quality craftsmanship evident throughout with 4-inch quarter sawn floors and Ivory Coast Coretec flooring in the lower level. Central A/C, gas fireplace, central vacuum, outdoor shower, irrigation system, surround sound stereo, and cedar closet. The exterior is equally impressive with carefully designed landscaping ensuring that something blooms from spring to fall, highlighted by a breathtaking Kousa Dogwood. A waterfront enthusiast's dream with a path to the beach and easy access to a mooring. And yes, there is room for a pool!

771 Fox Hill Road, Chatham

Listing courtesy of Listing Agent: Deborah Evans from Listing Office: Kinlin Grover Compass.

$6,495,000

5 Beds ⋅ 4 Baths ⋅ 73282917 MLS

70 Sears Point is a rare legacy property where Cape Cod history meets breathtaking beauty. Set on the bend of Oyster Pond River, and overlooking Stage Harbor, this generational estate offers 270-degree views, including the iconic Stage Harbor Lighthouse and the Atlantic beyond. Designed by Edward Sears Read, grandson of the renowned Willard T. Sears, and completed in 1940, this home harmoniously merges historical sophistication with modern craftsmanship. Antique wood paneling from 1600s Salem, and a nautical-inspired design, with the primary suite positioned like a ship's aft, create a unique treasure. The suite's balcony provides a secluded retreat and perfect perch for panoramic sunsets. The 'wheelhouse' below offers the perfect setting for evening cocktails, while additional living quarters provide space for family or guests. Set on over 200 feet of saltwater frontage with a private beach and licensed dock, the property invites invites you to connect with land and sea.

70 Sears Point, Chatham

Listing courtesy of Listing Agent: Tony Guthrie from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

$2,295,000

5 Beds ⋅ 2 Baths ⋅ 73282894 MLS

Discover the quintessential Cape Cod lifestyle in this charming 1940's Cape ranch, perfectly situated in one of North Chatham's most sought-after neighborhoods. This well-maintained home offers a blend of classic appeal and modern convenience, nestled among substantial and elegant residences. The serene setting provides a peaceful retreat moments from Scatteree Beach. Whether you're looking to enjoy the coastal breezes, explore the nearby Chatham Village, or simply relax in the comfort of your own backyard, this home offers endless opportunities for creating cherished memories.

504 Stony Hill Rd, Chatham

Listing courtesy of Listing Agent: Brian Pothier from Listing Office: Gibson Sotheby's International Realty.

$1,225,000

3 Beds ⋅ 3 Baths ⋅ 73282865 MLS

Sited on nearly an acre of land in Riverbay Estates, this spacious three bedroom, three bath home offers ample privacy and outdoor living space.Built in 1984 with an addition and updates in 2004, the home is designed with flexibility for one floor living with a generous sized first level primary suite withgas fireplace, walk in closet, and outdoor access. The kitchen features abundant cabinet space, a pantry, granite countertops and peninsula, and stainlessappliances including a gas range. The adjoining living room has a wood burning fireplace and two sliding doors to a 200 sf screened in porch and expansivedeck overlooking a private and sweeping yard suitable for family fun and potential for a pool. There is a formal dining room and mudroom with laundry andan additional full bath to complete the first floor. Above are two bedrooms with a shared full bath. The lower level offers 900 sf of finished space with mediaand an exercise area.

319 Riverview Dr, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$775,000

3 Beds ⋅ 2 Baths ⋅ 73282672 MLS

Welcome to 19 Stoughton Lane, Chatham, MA! Here's your chance to build the home of your dreams. Nestled south of Route 28 and just .02 miles to stunning Ridgevale Beach on Nantucket Sound, this prime location has so much potential. This property is a teardown but fear not! Included in the sale is a passing 3-bedroom Title V septic inspection report and Board of Health letter, ZBA approval to build a dwelling with a deck via special permit, and conservation approval. Seller has building plans for a 3 bedroom, 2 bath, 1,356 SF home. Imagine the possibilities with private outdoor space for your future garden oasis. Ready to create something special? 19 Stoughton Lane is the perfect location!

19 Stoughton Ln, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Kinlin Grover Compass.

$1,100,000

2 Beds ⋅ 2 Baths ⋅ 73282667 MLS

Welcome to 6 Palmer Drive, located in the sought-after area of Chatham, MA. This 2 bedroom, 2 bath 1,702 square foot ranch style home features one-floor living. Upon entering, you'll be greeted by an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas, creating an ideal space for entertainment. An additional great room with wood floors & a wood burning fireplace has a slider to a large deck. The large primary bedroom with ensuite full bath, additional bedroom, second full bath and laundry room complete the main floor living. Situated a half mile to Cow Yard beach & the Chatham Fish Pier and conveniently located .7 to the village for shopping, restaurants & the movies. Boasts a private yard, outdoor shower, and 2-car garage with storage area over the garage. Bring ideas to make this property your own while creating a relaxed lifestyle near all that Chatham has to offer. Please schedule your private showing today!

6 Palmer Dr, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Kinlin Grover Compass.

$824,000

2 Beds ⋅ 2 Baths ⋅ 73281584 MLS

Welcome to 22 Starfish Lane, a beautifully renovated oceanfront townhome nestled in the heart of Chatham. This fully furnished 2-bedroom, 2-bathroom home offers the epitome of Cape Cod living with breathtaking ocean views and private association beach access just steps from your door. Wake up to stunning sunrises over the water, as the airy, vaulted ceilings allow natural light to fill both bedrooms. Enjoy your morning coffee while watching the fishing vessels from your deck. Located just a short walk from the iconic Chatham Lighthouse and the vibrant seaport village, you’ll have easy access to dining, shopping, and entertainment. Explore the white sandy beaches, kayak along the coast, or take a leisurely stroll to local attractions. Great for families, friends and lucrative investment.

22 Starfish, Chatham

Listing courtesy of Listing Agent: Dawn Marie Boynton from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

$979,900

2 Beds ⋅ 3 Baths ⋅ 73279682 MLS

Discerning buyers will appreciate the 3 bath features and tranquil setting of this 2-bedroom, 3-bath condo on Perch Pond. The elegant décor, combined with the stunning water views creates a truly unique living experience. The open floor plan and upper level with water view offer endless possibilities for entertaining and relaxation, while your guests can enjoy their own private space. The finished lower level features a full bath designed with style and functionality for distinguished guests to enjoy. Seller Welcomes offers with requests for buyer concessions.

1076 Main St Unit 1076, Chatham

Listing courtesy of Listing Agent: Darci Sequin from Listing Office: Gibson Sotheby's International Realty.

$2,999,000

3 Beds ⋅ 3 Baths ⋅ 73276174 MLS

As you drive past Chatham light & turn right on Morris Island Rd, you will find yourself transported to a different time when things moved a little slower. You'll be surrounded by marshes & conservation land, popular with birders for its egrets, hawks & sandpipers. The 3BR, 3bath home sits on about a half-acre overlooking Stage Harbor to the west & the Atlantic to the east, which brings stunning sunrises & sunsets. To the south are acres for hiking, clamming, fishing, boating, you may dock your boat at Outermost Marina or moor your boat in ''the cove'' located just steps away from the home which features hardwood floors, beams, a gas fireplace & an open layout to take in all the views. The surrounding deck hugs the house w/a pergola, outdoor dining, outdoor shower, shed & fire pit. A large, private patio overlooks the family of ospreys who return every year to nest. Transform this home or renovate to suit your wildest dreams.

15 Edgewater Dr, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Kinlin Grover Compass.

$875,000

3 Beds ⋅ 3 Baths ⋅ 73279012 MLS

This immaculate and spacious colonial is privately set on a cul-de-sac! This beautiful home features a front to back living room with gas fired wood stove set in the fire place and double sliders to a sunny deck. A bright white on white eat in kitchen with light granite counters with sliders opening to a rear private deck is ideal for summer entertaining plus there is a formal dining room for family gatherings & holidays! The primary en-suite also runs front to back and is charming with a fireplace, private bath and walk in closet. Two other lovely bedrooms and center full bath finish the 2nd level. Hardwood floors are on the main and 2nd floors. A one car garage under with interior access to a full basement complete this home. Upgrades include: Town sewer, replacement Pella windows, decks redone with composit decking and railings, roof 3/2022,south side shingles 2021, garage door and opener 2023

53 Partridge Path, Chatham

Listing courtesy of Listing Agent: Kayla Hilts from Listing Office: Today Real Estate, Inc..

$1,929,000

3 Beds ⋅ 3 Baths ⋅ 73277907 MLS

Retreat lot in South Chatham. Nestled off Main Street and conveniently located mid-way between Chatham Village and Harwichport with their charming shops, galleries and fabulous restaurants and it is just minutes to several Nantucket Sound beaches! This custom home has so much to offer. The expansive open First Level has an oversized Great Room, Custom Cook's Kitchen, and a Large Dining Area with a WetBar along with a MudRoom with custom cabinetry, Powder Room and Pantry. The Second Level offers a gorgeous Primary Bedroom with walk-in closet, luxurious Ensuite Bath with marble Double Shower, Vanity and Water Closet. An adjacent Home Office which can do double duty as a Nursery, two large Family Bedrooms, Laundry Room, Family Bath AND a Bonus Room round out the Second Level! Attached is a large two-car Garage with plenty of room for storage as well as a huge yard and patio for family relaxation and space for a pool.Thinking of a Summer home or moving to the Cape? This could be the one!

4 Nickerson Circle, Chatham

Listing courtesy of Listing Agent: Pat Butler from Listing Office: Coldwell Banker Realty - Hingham.

$875,000

4 Beds ⋅ 3 Baths ⋅ 73277174 MLS

Nestled within the desirable Riverbay community in North Chatham, 470 Riverview Drive offers an exceptional blend of privacy and charm. Situated on a spacious corner lot, this property enjoys a prime location far from main roads, surrounded by mature trees and plantings that create a park-like setting. Built in 1972, the single-floor layout provides ample space for entertaining and flexibility. The authentic eat-in kitchen, adorned with a cheerful yellow palette, opens to a bright living and dining area with access to a large back deck, perfect for gatherings. The bedrooms are generously sized, with the primary suite featuring a slider to the deck. The expansive .91-acre lot includes a private fenced backyard and a partially finished walkout lower level, offering potential for additional living space. The second level also presents an opportunity for expansion. With room for a pool and the potential for modern updates, this home is an ideal canvas for creating your dream residence.

470 Riverview Dr, Chatham

Listing courtesy of Listing Agent: Tony Guthrie from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

$2,475,000

1 Beds ⋅ 2 Baths ⋅ 73275929 MLS

Location-Location-409 Main St. in Downtown Chatham offers you this very rare and desirable combination of a mixed use building with a 1st floor highly visible commercial space with showcase windows, maximum retail exposure and high foot traffic, as well as a fully renovated spacious apartment on the 2nd floor in the heart of Chatham Village. The property offers 5 private in-town parking spaces behind the building as well as the property is in the coveted GB1 zoning category which gives you the most versatile business options. The 1st floor commercial space has a fabulous open floor plan with 3 large room areas and four oversized windows right on Main St that will put your retail business right on the sidewalk. The 2nd floor apartment was fully renovated in 2019 and has one bedroom, full bath with laundry, an open floor plan with a kitchen and living room with vaulted ceiling and a large outdoor mahogany deck. Seller welcomes offers with requests for buyer concessions.

409 Main St, Chatham

Listing courtesy of Listing Agent: Rick Smith from Listing Office: Gibson Sotheby's International Realty.

$1,195,000

3 Beds ⋅ 2 Baths ⋅ 73275884 MLS

Welcome home to 3 Oyster Drive, a perfectly idyllic Chatham getaway! This enchanting cottage enjoys dazzling water views and a prime location near Outermost Harbor Marina, beaches, & Town. This 3 BR, 2 BA home is a blend of classic Cape Cod and some newer features and is the ideal backdrop to begin your own Chatham story. Many will find the home comfortable just the way it is, or choose to take advantage of approved house plans and construct an elevated new home on this one-of-a-kind site. First floor offers a bright living room with water views, beamed ceiling & fireplace. Small, functional kitchen with adjacent dining area. A bedroom, bath, and laundry are also on this level. Upstairs: full bath & 2 more BRS including the primary w/skylights & wall of glass to take in the view. On-demand gas hot water heater, outside shower, and a wrap-around patio with views. Walk to the beach, bike to Town, amazing rental potential, and water views. Sold mostly furnished; don't miss out!

3 Oyster Dr, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski from Listing Office: Kinlin Grover Compass.

$4,750,000

5 Beds ⋅ 8 Baths ⋅ 73275499 MLS

This impressive home sited on 2.07 acres on a quiet cul-de-sac is just a few minutes away from restaurants, the Chatham bike path and nearby Chatham beaches. The 2014 Eastward Companies home offers a tremendous sense of living space spanning 5,578 square feet and defined by lovely grounds, water views, luxurious finishes and a sweeping open floor plan. The main level flows seamlessly between the entrance hall, beautiful living room, sitting area, a fully equipped kitchen with walk-in pantry, resplendent primary suite with sitting room, mudroom and laundry. Above are three view-filled en suite bedrooms, bonus room and an expansive light-filled family room with fireplace and outdoor living room. The lower level standout feature is an entertainment retreat. This is an outstanding opportunity to own a welcoming retreat for family living and entertaining.

67 Uncle Alberts Dr, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$6,995,000

5 Beds ⋅ 7 Baths ⋅ 73270668 MLS

This exceptional custom residence currently under construction is situated in a prime North Chatham location with a nearby association beach. Seamlessly blending comfort and sophistication, the home spans three levels of generous open floor plan spaces and is located on over 1 acre. The main level interiors flow freely from foyer to a large great room with a living room, dining area and well appointed kitchen. There is a guest bedroom and ensuite bath, office and mudroom. Above is a luxurious primary suite with views of Crows Pond, Pleasant Bay and beyond and two additional en-suite bedrooms, laundry and loft area. The lower level accommodates a family room, exercise room and bath. The 4 BR main house is complemented by a detached garage with one bedroom guest quarters above. Replete with statement touches throughout, this home is designed for both family life and easy entertaining with a spa-like pool with hot tub. This inviting home is impeccably designed and a rare Chatham find.

16 Seapine Rd, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$4,250,000

5 Beds ⋅ 5 Baths ⋅ 73268604 MLS

On a tucked away street near town, beaches and some of Chatham favorite restaurants, this private hideaway on 1.4 acres transports you to a serene and sun-infused getaway overlooking a lush landscape of greenery and fabulous pond views. Custom design detail, soothing color palette and a sophisticated open floor plan make this home truly unique. A generous great room is anchored by a wood burning fireplace and a sweeping bank of southeastern facing windows and three french doors create seamless indoor outdoor flow. There is a Chef's kitchen with a large center island, nautical inspired bar area, cozy study, powder room and mudroom on the first floor. Upstairs a primary suite, and two additional bedrooms are on one wing and a large bedroom suite with private access on the other. An unfinished basement with abundant windows open to the outside to a poind-side backyard with pool potential. The home is compete with a charming guest cottage. Showings start Friday 7/26

43 Chatham Heights Road, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$4,495,000

4 Beds ⋅ 6 Baths ⋅ 73268296 MLS

Deeded rights to a boat slip in the Oyster River Hills Association's private neighborhood marina are just steps away. Custom builder Sears Point Residential has begun constructing a stunning new 4 bedroom, 6 bath, 4,908 Sq. Ft. classic Cape. Move in for the summer of 2025. The axis of the home is defined by a chef's kitchen with a Thermador six burner range, Thermador refrigerator, and additional beverage storage, a large center island with Quartz countertops, an open floor-plan dining and living space with hardwood floors, 9' plus ceilings and custom woodwork throughout. Each bedroom is en-suite with primary bedrooms with soaking tubs on both floors. A den/office, a mudroom, and an oversized one-car garage round things out. There is an additional 1,587+ sq ft of basement with high ceilings and deep window wells ready for customization. The irrigated yard is poised for generous outdoor living space and potentially a pool, ideal for entertaining family and friends.

45 Meadow View Rd S, Chatham

Listing courtesy of Listing Agent: The Bohman Hartung Group from Listing Office: Gibson Sotheby's International Realty.

$3,299,000

3 Beds ⋅ 3 Baths ⋅ 73262792 MLS

East, South, West.....180 degree water views over the Oyster Pond and the iconic church steeples in town. Dramatic waterfront home has undergone a full and complete renovation in 2024. The great room has commanding water views and steps out onto expansive wrap around deck. The chefs kitchen is equipped with high end appliances and a kitchen island that can seat a crowd. The primary suite offers a generous full bath and a walk in closet. The first level contains a family room, 2 more spacious bedrooms, one with a walk in closet and a separate laundry area. The first level steps out onto a lovely waterfront patio perfect for summertime entertaining. The lot has 180 ft of water frontage which allows for direct access to Oyster Pond for kayaking or paddle-boarding. Sited at the end of a private cul de sac, this lovely home offers peerless views and privacy. On demand Renai hot water heater heat pumps for heating and cooling, whole house generator. Landscaping going in soon!

127 Christopher Harding La, Chatham

Listing courtesy of Listing Agent: Kathleen Phelan from Listing Office: Compass.

$1,075,000

3 Beds ⋅ 3 Baths ⋅ 73260432 MLS

Deeded Access to stunning Lover's Lake, only a 3-minute walk! Welcome to 34 Horizon Drive, where coastal charm meets modern comfort. This delightful home offers 3 beds & 3 baths, perfect for those seeking community in Great Hill Estates. Step inside to discover a light-filled living space w/a seamless flow. A cook's kitchen w/stainless appliances w/gas stove, granite counters & ample cabinet space w/pantry w/washer/dryer hook-ups & dining area. A first story bedroom, full bath, deck & access to the oversized garage offer the possibility of one-floor living. The second story features a primary bedroom w/en-suite bathroom, walk-in closet & sitting room, providing a peaceful haven to relax & rejuvenate. An additional bedroom, full bath, laundry area & deck offer flexibility for guests. The walk-out level features a family room w/fireplace & outside patio space w/private yard. AC, 2017 roof & owned solar. Residents enjoy swimming, kayaking & paddle boarding at Lover's Lake.

34 Horizon Dr, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Kinlin Grover Compass.

$1,070,000

3 Beds ⋅ 3 Baths ⋅ 73260291 MLS

Welcome to 70 Uncle Deane's Road! This 3-bed, 2.5-bath post & beam home features stunning craftsmanship. South of Route 28, near the bike path & beaches. Step inside & be greeted by the charming hardwood floors & beautiful beams that flow seamlessly throughout. The open living room, dining area & kitchen make this home ideal for entertaining. The deck off the sunroom offers a private outdoor space, perfect for enjoying your morning coffee. The first story also has 2 bedrooms, 1 full & 1 half baths & a great room which has been an artist's studio. The studio space would be an amazing area for a 1st floor primary suite, bring your ideas. The second story begins with a cool loft area, then the primary suite, an office & additional loft space w/balcony. But the real showstopper? The private landing on Taylor's Pond, w/storage for your kayaks & canoes. Failed septic, design & install of new system is the buyer's responsibility. New roof, shed, 1-car garage & gas heat. So much to enjoy!

70 Uncle Deanes Rd, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Kinlin Grover Compass.

$6,250,000

2 Beds ⋅ 3 Baths ⋅ 73259203 MLS

Overlooking beautiful Crows Pond, this exquisite property offers a myriad of opportunities with a 6 BR septic and conceptual plans for a 4 BR residence, an existing two bedroom, two bath home that feels like a private sanctuary and exudes a perfect blend of luxury living with an elegant coastal charm. Located on 1.8 acres across from Eastward Ho Country Club, the property offers a multitude of expansion opportunities. The home highlights custom craftsmanship and detailed finishes and provides ample space for intimate or large gatherings with generously proportioned indoor and outdoor living spaces. The great room with gas fireplace and dining room are view-filled and adjoin a sunroom with a wood burning fireplace. The kitchen has all the amenities as well as a sitting area that opens to a patio with a fire pit. The bedrooms afford privacy with a first floor primary suite and a second level sitting room and en suite bedroom-all with water vistas. This home is a perfect Chatham retreat.

372 Fox Hill Rd, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$2,495,000

3 Beds ⋅ 4 Baths ⋅ 73258903 MLS

Immerse yourself in the ultimate beach lifestyle. Superbly located in a highly desirable Lighthouse Beach neighborhood, this luxurious beach house built in 2018 was extensively refreshed in 2023 with all new bathrooms, appliances, light and plumbing fixtures, smart technology and exterior curb appeal. The interiors are both elegant and playful offering a timeless coastal character. The home brings the outside in with the multi-level deck areas and view filled living spaces. The main level great room has a seaside vibe with nautical touches, fireplace, wood floors and a fully equipped kitchen with a quartz center island and backsplash in calming shades of blue. Wrap around windows frame the sitting area that opens to the main level. There is also a private en suite bedroom. Above is an additional en suite bedroom, laundry and a primary suite with a private study/sitting room, fireplace and deck with spectacular Chatham Harbor sunrises. A short stroll to Lighthouse Beach.

16 Little Beach Rd, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$3,695,000

6 Beds ⋅ 5 Baths ⋅ 73258132 MLS

Architectural perfection meets natural harmony in this stunning Polhemus Savery DaSilva (PSD) home. Tucked quietly within the desirable North Chatham neighborhood with beach access on Pleasant Bay, a short stroll away, the residence offers a modern twist on the classic shingle style architecture and delivers impeccable craftsmanship, custom millwork, and exquisite stonework to create a truly refined family home. Prepare to be captivated by the southeastern exposure that envelops the main living spaces. The contemporary open floor plan, welcomes privacy for both large and small family living with a multilevel floor plan with five dedicated generously sized bedrooms and three and half baths, but also accommodates one floor living with a main level primary suite.

173 Kendrick Road, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$2,395,000

3 Beds ⋅ 3 Baths ⋅ 73258530 MLS

Waterfront onTaylor's Pond, a saltwater inlet with access to Nantucket Sound. This hidden jewel is tucked down a long drive. Quality craftsmanship is evident throughout this 3BR plus den, 2.5 bath contemporary Cape renovated in 2017-2018. Old growth black walnut flooring throughout the first floor creates a bold backdrop for the open floorplan. Chef's kitchen with granite counters, induction stove and wet bar open on to a dining area overlooking the water. Adjacent living room with cozy fireplace and "hidden" study are just the beginning. Three second floor bedrooms, one a primary suite with private bath, provide ample accomodations. A walk out lower level office/yoga studio,has views as well as access to the outdoor shower. Large oversized deck and entertaining shed are additional highlights. Coastal gardens surround and when not kayaking fromyour back yard, three Nantucket Sound beaches are in close proximity.

2519 Main St, Chatham

Listing courtesy of Listing Agent: Lori Fanning Smith from Listing Office: Compass.

$1,995,000

1 Baths ⋅ 73258353 MLS

Zoned Gb3 this great commercial, multi-use property consists of 2 buildings.The first building built in1995 has 948 sf with a full bath and office, 2 gas heaters, and a Viessman heating and hot water system and a full basement. The second building has 1,638 sf built in 2003 and has 2 bays and a carport with a second floor ready to finish and the first floor has a gas heater. Lots of possibilities. Documents include Gb3 standard permitted uses, section 3.4 and Appendix 1 ''Schedule of Use Regulations'' and septic site plan. Great opportunities-previously a builders work shop and warehouse for storing automobiles, boats, vintage motorcycles etc. The solar panels are owned. In the GB3 zone with a special permit residential may be allowed. Please verify all information contained herein. Don't miss this special property!

231 Crowell Road, Chatham

Listing courtesy of Listing Agent: Judith Smith from Listing Office: John C. Ricotta & Associates, Inc..

$1,699,000

3 Beds ⋅ 4 Baths ⋅ 73257136 MLS

''Moongazer'' represents a rare opportunity to purchase a thoughtfully updated, proven income producing property with deeded access to Taylor's Pond where it is a fun and easy kayak or paddle board out to Nantucket Sound and the beach. This 3,150 sq ft split-level house offers far more living space and room for overflow guests than meets the eye. Upon entering the house, you will be wowed by the soaring ceilings, streaming natural light, two-sided corner gas fireplace, hardwood floors, and updated kitchen. The 2023-built bluestone patio and wood-burning stone fireplace have transformed the outdoor living space into a magnificent evening gathering place. The 2nd floor consists of an ensuite primary bedroom and two generous bedrooms that share a full bath. The unique split level design includes a large family room with a balcony and a study with a full bath on the third floor. A few steps down from the living room is 432SqFt of finished lower level space with a full Bath and laundry room

46 Juniper Ln W, Chatham

Listing courtesy of Listing Agent: The Bohman Hartung Group from Listing Office: Gibson Sotheby's International Realty.

$2,595,000

4 Beds ⋅ 4 Baths ⋅ 73256437 MLS

Don't miss this fabulous home which is part of Harbor Coves Assoc.with association rights to Crows Pond a saltwater pond leading out to Bassing Harbor, Ryder's Cove, Pleasant Bay, Chatham Harbor and the Atlantic. Assoc. beach rights and mooring field just down the street. This 3900 sf home provides 4 bedrooms 3 and 1/2 baths and has plenty of extra space for family and friends. Wonderful family room with cathedral ceiling, wet bar and spacious living room with built-ins and woodburning fireplace. There is a dining room just off the kitchen with wood floors, built-in corner cabinets and fireplace fueled by propane. The first floor den or office is perfect for those that are able to work from home. The second floor has a large loft with built-in window seat and a beautiful Palladian window allowing light to fill the room with 2 generous sized bedrooms and a full bath finishing off the second floor. The home has town water and a well for irrigation. Please verify all information contained

174 Seapine Road, Chatham

Listing courtesy of Listing Agent: Judith Smith from Listing Office: John C. Ricotta & Associates, Inc..

$4,695,000

3 Beds ⋅ 3 Baths ⋅ 73256075 MLS

Nestled in Hardings Beach Hills, Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, presents a stunning display of nature with its panoramic marsh and creek views. The architecture of this residence is a masterful fusion of classic Cape vernacular with modern inspiration, reflective of PSD’s signature style. Views of the marsh, creek and surrounding landscape are offered from every window yet the focus of this extraordinary home is the two story dining room and open reading nook above, illuminated by a dramatic wall of windows overlooking the marsh. The main level includes a chef's kitchen, bedroom/study, full bath and multi-use mudroom. Above is a serene en-suite primary bedroom, a guest bedroom and sitting room. The walk-out lower level offers additional living space and laundry. The stunning marsh and creekfront setting is augmented by mature plantings, natural stonework. This coastal home is part of the Bucks Creek Association with a community dock for kayaking.

30 Indian Trail, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$13,950,000

7 Beds ⋅ 7 Baths ⋅ 73251537 MLS

Situated on a bluff with commanding views over Chatham Harbor, North Beach, and the Atlantic beyond, this extraordinary offering stands as one of the most significant estate properties on exclusive Shore Road. A short stroll from everything Chatham Village has to offer, the property boasts an unprecedented 2.86 acres with rolling lawns, mature landscaping, and a private sandy beach. Mesmerizing views take center stage immediately upon entering the residence, with gracious living spaces and exquisite architectural details. Fit for everyday living and grand entertaining, thoughtful scale and proportions are evidenced throughout. From a large seaside terrace to a secluded deck just above the harbor, numerous outdoor living areas are found across the park-like grounds with ornamental trees and gardens. Set in one of New England’s most sought-after waterfront communities, this exceptional estate delivers an unsurpassed lifestyle.

552 Shore Rd, Chatham

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

$749,000

3 Beds ⋅ 2 Baths ⋅ 73242439 MLS

A pleasant surprise when you walk into this home to find beautiful structural beams in the dining area, family room and primary bedroom , gleaming hardwood floors and an open family, dining and kitchen area. A slider and French door leading to the decks which allows all the sunshine in. Although not remodeled, this home appears to be in good condition which needs some repairs, mostly exterior. Being offered in '' as is'' condition with the exception of a passed septic inspection and updated smoke detectors. Seller welcomes offers with requests for buyer concessions.

135 Holly Drive, Chatham

Listing courtesy of Listing Agent: Darci Sequin from Listing Office: Gibson Sotheby's International Realty.

$1,295,000

3 Beds ⋅ 3 Baths ⋅ 73242236 MLS

First time on the market! Experience coastal living surrounded by conservation areas and stunning sunsets. This remarkable Chatham year-round retreat spans 2.1 waterfront acres along the Monomoy River. The main house features single-story living with two bedrooms, cozy living areas, bonus area and captivating outdoor garden spaces. The late 1800’s original cottage offers the opportunity to be a second dwelling or an additional bedroom with half bath and scenic water views from every window including the cedar outdoor shower. Updates include new air conditioning, appliances, water heater, beautiful refinished oak floors, and custom millwork. Nestled down a picturesque shell drive, enjoy kayaking from your own water's edge with private access leading out to Pleasant Bay. Seller welcomes offers with requests for buyer concessions.

1174 Old Queen Anne Rd, Chatham

Listing courtesy of Listing Agent: Paul McCormick from Listing Office: Gibson Sotheby's International Realty.

$12,500,000

5 Beds ⋅ 6 Baths ⋅ 73241325 MLS

Set in the heart of Chatham Village, yet a world apart, 23 Oyster Pond Lane offers an extraordinary lifestyle in one of New England’s most sought after communities. Hidden behind tall hedges, a winding driveway gives way to park-like grounds with manicured gardens and mature trees that set the stage for an inimitable seaside estate. Grand and inviting, the five-bedroom colonial residence is ideally perched on a bluff with panoramic views of Oyster Pond and Chatham Village. The interiors artfully balance old world craftsmanship and modern luxury with exquisite attention to detail throughout. At the heart of the home, a gourmet kitchen caters to indoor and outdoor living with French doors that open to a waterside terrace and swimming pool. The well-appointed primary suite is accessed via a private staircase, complete with a walk-in closet, study, and en suite bathroom.

23 Oyster Pond Ln, Chatham

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

$5,950,000

5 Beds ⋅ 7 Baths ⋅ 73232841 MLS

Escape to unparalleled luxury living in Chatham! This meticulously crafted architectural gem offers a blend of modern sophistication & coastal charm with deeded beach rights & access to Chatham's pristine waterways. Classic entryway welcomes you into a chef's kitchen and spacious living room adorned with westerly views of Ryder's Cove. Expansive windows and glass doors fill the space with natural light seamlessly integrating indoor and outdoor areas, an expansive deck, patio and inviting pool, perfect for entertaining or relaxing in style. Ascend via the elevator to discover 4 luxurious en-suite bedrooms on the second floor, each appointed with walk-in closets. The primary ensuite boasts a spa like bathroom & private deck. The finished walk-out lower level, offering versatile spaces for wellness area, bunk accommodations or playroom. The guest house with kitchenette, living area, bedroom ensuite overlooks the saltwater pool. Sellers welcome offers with requests for buyer concessions.

51 Cove Hill Rd, Chatham

Listing courtesy of Listing Agent: Betsy Hargreaves from Listing Office: Gibson Sotheby's International Realty.

$2,900,000

4 Beds ⋅ 4 Baths ⋅ 73237523 MLS

Introducing this 4-bedroom, 3.5-bathroom home on Stage Neck Rd! This property offers 3834 sq ft of living space on a generous 44212 sq ft lot. Embrace the bright living room with vaulted ceilings, a fireplace, and French doors leading to a large deck and an enclosed porch. Access to a shared boat house along the Oyster River adds to the allure. With a spacious great room, a study, a master bedroom on the first level, an ensuite on the second floor, and two additional bedrooms and a bath, this home exudes versatility and elegance. Don't miss the chance to make this property your own!

106 Stage Neck Rd, Chatham

Listing courtesy of Listing Agent: Jen Graham from Listing Office: Kinlin Grover Compass.

$3,149,000

3 Beds ⋅ 5 Baths ⋅ 73232947 MLS

In-town Chatham, 2018 custom-built home with room for a pool on a quiet lane a short stroll to village shops, restaurants, and Angler's baseball. This 3 BR, 4/1 Baths, 4,100 sf home is full of thoughtful upgrades including walnut hardwood floors, an office, a 3-season porch, bonus sleeping areas for overflow guests, finished lower level, 3-zone natural gas heating/AC, two tankless water heaters, whole house generator, Sonos sound system, outdoor shower, cobblestone driveway and stone patio surrounded by mature privacy plantings and irrigation. The open first-floor plan centers around a chef's kitchen with an oversized island, granite, gas range, and pantry, a dining room & living room with custom cabinets, and a gas fireplace. Also on the first floor are an ensuite bedroom, mudroom, and laundry. The primary suite is on the 2nd floor along with the third bedroom and a sleeping loft. The finished lower level features a media room with surround sound, recreation area and 1/2 bath.

25 Glover Square, Chatham

Listing courtesy of Listing Agent: The Bohman Hartung Group from Listing Office: Gibson Sotheby's International Realty.

$1,199,000

2 Beds ⋅ 3 Baths ⋅ 73230934 MLS

“High Noon” is a turnkey summer retreat and profitable investment property in one of Chatham's most sought-after Nantucket Sound beach neighborhoods. Thoughtfully updated in 2022, it is only .3 mi from Ridgevale Beach. Stepping inside, you will be greeted by a cozy sun-filled enclosed front porch that leads into the open living and dining room with fir hardwood floors. The home has central A/C and natural gas. The stunning kitchen has quartz countertops, and stainless-steel appliances, including a 6-burner Wolf gas stove, retro refrigerator and wine cooler. It opens to a large deck, perfect for outdoor dining and entertaining. The first floor also features a bedroom, full bath and laundry. The spacious second-floor primary en-suite bedroom has a luxurious new full bath. The separately accessed lower-level walk-out offers bonus rooms and a full bath. Between the close proximity to Ridgevale Beach and Chatham’s village shops, it is no wonder “High Noon” has such a stellar rental history.

249 Ridgevale Road, Chatham

Listing courtesy of Listing Agent: The Bohman Hartung Group from Listing Office: Gibson Sotheby's International Realty.

$5,495,000

2 Beds ⋅ 3 Baths ⋅ 73208512 MLS

Welcome to "My Oyster" a custom-built 2-bedroom, three-bath guesthouse with cherry cabinets, maple and cherry trim, wide pine and hardwood floors, wainscoting, and crown molding, creating a luxurious ambiance of warmth and tranquility. A Dutch oven satisfies culinary desires, and the great room next to the two-car garage can serve as an office, gym, or game room. High on a bluff, My Oyster's decks offer a 180° view of Oyster Pond, Stetsons Cove, and the Oyster River out to Nantucket Sound. This historic 1.4-acre waterfront estate, once part of Chatham Bars Inn's farm, has been cherished by the same family for over 70 years. The 60,000-square-foot lot supports the potential for a custom four-bedroom dream home, tennis court, or pool. A Post and Beam barn with water and electricity makes a great workshop or man cave. Accessible via a scenic driveway, the property offers tranquility, privacy, and timeless charm. Seller welcomes offers with requests for buyer concessions.

99 Uncle Alberts Drive Extension, Chatham

Listing courtesy of Listing Agent: Rick Smith from Listing Office: Gibson Sotheby's International Realty.

$1,699,000

3 Beds ⋅ 3 Baths ⋅ 73189233 MLS

Incredible spot...Tucked away at the end of a private road and only a short distance to Cockle Cove beach, this 3 bedroom 2 1/2 bath home with long leaf yellow pine floors throughout the first floor has plenty of living space for family and guests. Surrounded by an expansive wrap-around deck, the open concept first floor is highlighted by the living room with wood burning fireplace, inviting dining area and kitchen with large island & Corian countertops, as well as a sunroom that is filled with light and a den — all of which make this home a delight to show. The second floor includes a large primary bedroom with en suite bath & bonus room attached, two more bedrooms with a shared full bath & three separate decks to enjoy the fresh salt air. The lower level, with a slider overlooking the idyllic woods to the east, is just waiting to be finished. Don't miss seeing this special property. Rentals in place for the summer of 2024. Please verify all information contained herein.

70 Lantern Lane, Chatham

Listing courtesy of Listing Agent: Judith Smith from Listing Office: John C. Ricotta & Associates, Inc..

$1,995,000

3 Beds ⋅ 2 Baths ⋅ 73173992 MLS

Move In Ready and Offered Mostly Furnished - Three bedrooms, 2 baths, lushly landscaped and very private lot. Title V 4 bedroom septic system on over one acre. Tranquility abounds at this idyllic Cape Cod property which must be seen to be truly appreciated. Entertain or just relax on the oversized mahogany deck with breathtaking, southwesterly views over Seaquanset Cove and out to Nantucket Sound. Open kitchen/ family/ dining room with cathedral ceiling and a gracious, large living room with fireplace. Main floor includes a primary bedroom and full bath. Lower level is walkout and includes a bathroom between two oversized and flexible finished rooms (one with a fireplace), laundry room, and utility/ storage room. One car, easy access, attached garage. A special home and private property in a quiet neighborhood. Memories will be made here in every season. Come live the Chatham lifestyle!

17 Geranium Dr, Chatham

Listing courtesy of Listing Agent: Cheryle Young from Listing Office: Today Real Estate, Inc..

$6,500,000

9 Beds ⋅ 11 Baths ⋅ 73167525 MLS

Landmark Main Street Chatham mid-19th century Victorian thoughtfully restored inside and out by renowned architects and builders Polhemus Savory DaSilva. The detailed restoration of this quintessential five bedroom Italianate included a new kitchen, plumbing, electrical system, air conditioning, rebuilding the four and half bathrooms, primary suites on both the first and second floors and outdoor patio with gas fire pit and Admiral Charles Rockwell's iconic eight sided shingled gazebo. In 2010, the Chatham Historical Society honored the work with its prestigious Chatham Preservation Award. This offering also includes an adjacent property highlighted by a renovated barn with a two car garage, extra storage, a gym, large recreation room with a deck and a full bath attached to a thoughtfully renovated four bedroom, 3.5 bath house with an updated kitchen, open floor plan, two en suite bedrooms with private bathrooms, gas fireplaces and screen porches, a home office and ample parking.

326 - 324 Main Street, Chatham

Listing courtesy of Listing Agent: The Bohman Hartung Group from Listing Office: Gibson Sotheby's International Realty.

$1,500,000

3 Beds ⋅ 4 Baths ⋅ 73147436 MLS

Enjoy a private setting in this immaculate move in ready 3 Br, 3.5 bath home.! This comfortable 3852 square foot home with high ceilings and an open floor plan, features granite countertops in a large kitchen and dining area. Lower level is included in total living space. Additionally very adequate living room w/fireplace, a first floor primary bedroom with bath, and a den, tv room or home office, all on the first floor. Also on the first level is a mudroom with laundry room and full bath. On the second level there are two large bedrooms, and a full bath with double vanity. Other features include a recently updated Tesla Solar Electric System with 65 panels, a recently updated heating and A/C system including hot water tank and a recently renovated mahogany deck overlooking a wooded area. The walk out lower level is an area to be developed for additional living space featuring high ceilings and is very spacious. This must be seen to appreciate,

355 Training Field Rd, Chatham

Listing courtesy of Listing Agent: Harry Cutts from Listing Office: William Raveis Chatham.

$7,250,000

10 Beds ⋅ 10 Baths ⋅ 73136354 MLS

Beautiful Chatham Georgian estate on 1.3 acres within walking distance to the center of town, Oyster Pond beach and all the amenities Chatham has to offer. Spectacular sunset views of the Oyster Pond, rolling lawns, bluestone patios and specimen landscaping surround this magnificent estate in the heart of downtown. Comprised of 10 bedrooms, 7 fireplaces, 7 full and 3 half baths, elevator and approximately 8000 square feet of living space on 3 main levels, with a grand main foyer and cantilevered staircase. The lower level includes a speakeasy bar and playroom. North and south wings of this single family home provide separate quarters for guests or family-each with 3 bedrooms, living areas and kitchens. A Chatham landmark, ''The Beechwood'' reflects unparalleled architectural detail, craftsmanship and timeless charm-perfect for large family gatherings of multiple generations under one roof.

150-154 Cross Street, Chatham

Listing courtesy of Listing Agent: Timothy Bailey from Listing Office: John C. Ricotta & Associates, Inc..

$9,995,000

6 Beds ⋅ 8 Baths ⋅ 73124636 MLS

Absolute perfection at this stunning in-town compound featuring commanding water views over Oyster Pond! The result of a multi-year collaboration by top architects, designers and builders, this sophisticated and turn-key coastal offering seamlessly blends classic and contemporary elements to create a one-of-a-kind retreat. Walls of glass overlook expansive lawns and gardens, while sun-drenched living spaces set the stage for large scale entertaining, or relaxed everyday living, alike. Top of the line systems and amenities are found throughout the thoughtfully designed 5 bedroom main house, while a 3 story guest house provides additional accommodations overlooking the beautiful pool and spa. Immediate access to the beach, with a private association dock, and just steps to the restaurants, shops and galleries of Chatham’s quintessential Main Street, this exclusive offering is a must see, by appointment only.

178 Queen Anne Rd, Chatham

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

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