Pending Listings in South Brewster, MA

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PENDING

ABOUT THIS HOME
Pending Listing in South Brewster, MA:
Tucked away in a great location yet close to downtown Orleans, Brewster, Chatham, and Pleasant Bay area. This charming three-bedroom, two-bath Cape-style ranch combines comfort and convenience. Recent updates include a 2022 CertainTeed Pro roof, pressure-treated deck, and Gutter Helmet system. The front garden showcases mature azalea, lilac, and other flowering shrubs, plus a serene goldfish pond with a granite Japanese lantern. Relax or entertain on the spacious back deck with great privacy. Inside, enjoy oak hardwood floors, Armstrong luxury vinyl in the kitchen and baths, and a cozy gas fireplace with fan and thermostat. Renewal by Andersen tilt-in windows and an Andersen slider offer ea

$650,000

3 beds2 baths1,188 sq ft

171 Timberlane Dr, Brewster, MA 02631

0.35 acre lot • Garage • Car-dependent

PENDING

ABOUT THIS HOME
Pending Listing in South Brewster, MA:
An exceptionally rare offering where coastal charm meets comfort in the highly desired Sheep Pond Estates. A short stroll through the neighborhood offers you deeded beach access to a private association beach on Sheep Pond, where sandy shores, boating and fishing opportunities await. This delightful well-maintained ranch-style home with a tastefully finished lower level offers the perfect blend ofindoor and outdoor living across 1,800 square feet of thoughtfully designed space. Step into a welcoming fire-placed living area that flows seamlessly to the dining area with access to a large deck ideal for entertaining family and friends. Notable are the hardwood floors throughout and the stylish

$740,000

3 beds1 bath1,800 sq ft

33 Captain William Arthur Rd, Brewster, MA 02631

0.47 acre lot • $17 HOA • Garage

PENDING

ABOUT THIS HOME
Pending Listing in South Brewster, MA:
''The Best View of Sheep Pond. '' That's what the neighbors say--and once you see it, you'll understand why. Tucked down a long, private driveway sits this five-bedroom, two-bath classic, owned by one family for 58 years. The home blends warmth, natural light, and timeless character with a layout designed for generations to enjoy. A cathedral-ceilinged living room, the dining area, and the kitchen all look out toward the pond. Downstairs, a sprawling walk-out basement offers incredible flexibility, complete with a second fireplace, a spacious den, and a fully functional second kitchen. The outdoor living space is just as compelling. You've got your own little piece of Sheep Pond with a priv

$1,300,000

5 beds2 baths2,599 sq ft

242 Sheep Pond Dr, Brewster, MA 02631

0.53 acre lot • $18 HOA • Car-dependent

PENDING

ABOUT THIS HOME
Pending Listing in South Brewster, MA:
Welcome to this charming, well-maintained 3-bedroom, 2.5-bath home, situated on a peaceful lot set well back from the road. Built in 1985, this home combines timeless charm with modern updates. Step inside to discover a cozy living room with fireplace and gleaming hardwood floors that flow throughout the home. The updated eat-in kitchen is move-in ready with stainless appliances and granite counters. The primary bedroom is complete with its own private full bath, two additional bedrooms and another full bath provide plenty of space for family or guests. The main level also features a convenient ground floor laundry and a dedicated drop zone, making daily life a breeze. The incredible outdoo

$779,000

3 beds2.5 baths2,084 sq ft

1437 Long Pond Rd, Brewster, MA 02631

0.58 acre lot • Garage • Car-dependent

PENDING

ABOUT THIS HOME
Pending Listing in South Brewster, MA:
Set on an 1-acre lot in a quiet wooded neighborhood, this spacious Cape Cod home offers nearly 3,000 sq ft of living space, on top of an additional potential 1000+ sqft of unfinished basement that could be finished. Ideal for entertaining, it features all on the 1st floor: an open kitchen with an island & a slider connecting to a big deck, a huge vaulted ceiling family room with another slider leading to the same deck & the spacious yard with wood views, a living room & dining area, a 2nd bedroom/den/home office, a full bath. The 1st floor also has a laundry room and a large primary bedroom suite with private full bath, double vanity & big walk-in closet. The 2nd flo

$999,000

4 beds3 baths2,964 sq ft

393 Thousand Oaks Dr, Brewster, MA 02631

0.97 acre lot • 2 garage spots • Car-dependent

Property at 272 Sheep Pond Dr, Brewster, MA 02631, 3 beds, 2 baths

$849,000

3 beds2 baths1,764 sq ft

272 Sheep Pond Dr, Brewster, MA 02631

Property at 737 Thousand Oaks Dr, Brewster, MA 02631, 2 beds, 2 baths

$420,850

2 beds2 baths1,302 sq ft

737 Thousand Oaks Dr, Brewster, MA 02631

Property at 37 Oliver Rd, Brewster, MA 02631, 4 beds, 3.5 baths

$2,695,000

4 beds3.5 baths3,937 sq ft

37 Oliver Rd, Brewster, MA 02631

Property at 26 Newport Rd, Brewster, MA 02631, 5 beds, 2 baths

$729,000

5 beds2 baths1,344 sq ft

26 Newport Rd, Brewster, MA 02631

Property at 958 Long Pond Rd, Brewster, MA 02631, 4 beds, 3 baths

$1,120,000

4 beds3 baths2,440 sq ft

958 Long Pond Rd, Brewster, MA 02631

Property at 663 Crowells Bog Rd, Brewster, MA 02631, 4 beds, 3.5 baths

$1,589,000

4 beds3.5 baths3,738 sq ft

663 Crowells Bog Rd, Brewster, MA 02631

Property at 33 Rogers Rd, Brewster, MA 02631, 2 beds, 2 baths

$875,000

2 beds2 baths2,024 sq ft

33 Rogers Rd, Brewster, MA 02631

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CONTINGENT

ABOUT THIS HOME
Pending Listing in South Brewster, MA:
Ocean Edge Resort - Renovated 1st-Floor Condo, Turnkey & Furnished! Exceptional value in Brewster's premier Ocean Edge Resort with world-class amenities and beautifully maintained grounds. This fully renovated 2-bedroom, 2 full-bath first-floor condo is a turnkey rental investment or ideal year-round/vacation home. Sold fully furnished, it features newer flooring, appliances, updated kitchen cabinets, counters, and stylishly renovated bathrooms. The spacious primary suite offers a full en-suite bath, newer A/C, and a new window. Enjoy a large flatscreen TV, full-size washer/dryer, and sliders to your private patio with peaceful golf course views. Resort amenities include indoor/outdoo

$429,000

2 beds2 baths935 sq ft

88 Eaton Ln #88, Brewster, MA 02631

$425 HOA • Car-dependent

CONTINGENT

ABOUT THIS HOME
Pending Listing in South Brewster, MA:
This 2 bedroom, 2 full bath first-floor condo in Ocean Edge offers easy living with a walk-out patio perfect for dining al fresco while enjoying the lush, landscaped surroundings by the golf course. Inside, the updated kitchen features fresh white cabinetry, butcher block countertops, and a charming coffee bar. The open-concept dining and living areas create a welcoming space for entertaining. Some rooms have just been freshly painted and a brand new water heater will give you peace of mind. The condo is offered turn-key for immediate enjoyment. Located in the heart of Brewster, you'll have access to all the town has to offer—nearby Brewster Flats at the bayside beaches, restaurants a

$395,000

2 beds2 baths935 sq ft

38 Eaton Ln #38, Brewster, MA 02631

$415 HOA • Car-dependent

CONTINGENT

ABOUT THIS HOME
Pending Listing in South Brewster, MA:
Discover peace and privacy in this South Orleans retreat. On nearly an acre, this property is completely surrounded by hundreds of acres of conservation land—yet is just minutes from village shops, bays, beaches, and all Orleans has to offer. The home welcomes you with a sun-filled, open-concept first floor where the kitchen, dining, and living areas create the perfect gathering space. A first-floor bedroom, and separate half bath with laundry, and versatile mudroom add convenience and flexibility. Upstairs, you will find generous sized primary bedroom as well as two additional bedrooms and a shared full bath. The lower level with high ceilings offers potential to expand your living a

$850,000

4 beds1.5 baths1,846 sq ft

37 Eli Rogers Rd, Orleans, MA 02653

0.92 acre lot • Car-dependent

PENDING

ABOUT THIS HOME
Pending Listing in South Brewster, MA:
Set in the heart of Brewster, one of Cape Cod's most beloved towns, 30 Fox Crossing offers a rare opportunity to create the perfect retreat. With its desirable location near bay beaches, conservation trails, and charming village life, this property captures the essence of Cape Cod living. Designed with an open floor plan, the home invites connection and ease of living. Spacious living areas flow seamlessly into one another, creating a welcoming environment for gatherings of all sizes. Outdoors, the private backyard is a true extension of the home, complete with an in-ground pool, fire pit, and ample space for summer entertaining. While the residence offers a strong foundation and a sought-a

$895,000

5 beds3 baths3,304 sq ft

30 Fox Crossing Rd, Brewster, MA 02631

1.38 acre lot • $17 HOA • 2 garage spots

PENDING

ABOUT THIS HOME
Pending Listing in South Brewster, MA:
Welcome to 41 Great Oak Road in Brewster. Built in 1974, this traditional Cape has four bedrooms, two bath, a one car garage and sits on . 61 acres. The floor plan is two bedrooms & a full bath on each level. The spacious eat in kitchen leads to a large deck and very private yard, including a shed! There is a full, freshly painted walk out basement. This home is close to the Brewster General Store, Cape Cod Bay beaches & a number of fresh water ponds.

$675,000

4 beds2 baths1,789 sq ft

41 Great Oak Rd, Brewster, MA 02631

0.61 acre lot • $17 HOA • Garage

PENDING

ABOUT THIS HOME
Pending Listing in South Brewster, MA:
Charming 3-bedroom Custom Cape-Great Investment Opportunity Near Scenic Ponds and Bike Trail. Whether you are looking for ideal rental income or a year round home, this property is a gem. Tucked off route 124, it offers over an acre of privacy and backs up to town land. A peaceful setting while being steps away from 3 picturesque ponds, ideal for swimming, boating or simply relaxing by the water. Hop on the bike trail, directly across the street, and travel from Yarmouth to Wellfleet. This thoughtfully crafted 3-bedroom, 2.5-bath custom build offers charm, functionality and location. The main floor features an open concept living and dining area, large kitchen, half bath with laundry and su

$735,000

3 beds2.5 baths1,963 sq ft

1080 Harwich Rd, Brewster, MA 02631

1.38 acre lot • 2 garage spots • Car-dependent

Property at 85 Yankee Dr, Brewster, MA 02631, 3 beds, 2 baths

$705,000

3 beds2 baths1,192 sq ft

85 Yankee Dr, Brewster, MA 02631

Property at 21 Nancys Way, Brewster, MA 02631, 3 beds, 2.5 baths

$1,250,000

3 beds2.5 baths2,480 sq ft

21 Nancys Way, Brewster, MA 02631

Property at 19 Burning Bush Way, Brewster, MA 02631, 2 beds, 2 baths

$750,000

2 beds2 baths2,034 sq ft

19 Burning Bush Way, Brewster, MA 02631

Property at 34 Uncle Israel Rd, Orleans, MA 02653, 2 beds, 2 baths

$650,000

2 beds2 baths1,346 sq ft

34 Uncle Israel Rd, Orleans, MA 02653

Property at 105 Middlecott Ln Unit 105, Brewster, MA 02631, 2 beds, 2 baths

$649,900

2 beds2 baths1,190 sq ft

105 Middlecott Ln Unit 105, Brewster, MA 02631

Property at 27 Mill Pond Rd, Harwich, MA 02645, 2 beds, 1 bath

$649,000

2 beds1 bath1,188 sq ft

27 Mill Pond Rd, Harwich, MA 02645

Property at 6 Sturbridge Dr, Orleans, MA 02653, 3 beds, 2 baths

$1,299,000

3 beds2 baths2,400 sq ft

6 Sturbridge Dr, Orleans, MA 02653

Property at 159 Old Chatham Rd, Brewster, MA 02631, 3 beds, 2 baths

$750,000

3 beds2 baths1,680 sq ft

159 Old Chatham Rd, Brewster, MA 02631

Property at 61 Fletcher Ln Unit H, Brewster, MA 02631, 1 bed, 1 bath

$295,000

1 bed1 bath579 sq ft

61 Fletcher Ln Unit H, Brewster, MA 02631

Property at 193 Quanset Rd, Orleans, MA 02653, 4 beds, 3 baths

$2,500,000

4 beds3 baths3,843 sq ft

193 Quanset Rd, Orleans, MA 02653

Property at 152 Pleasant Bay Rd, Harwich, MA 02645, 5 beds, 4 baths

$1,649,900

5 beds4 baths4,308 sq ft

152 Pleasant Bay Rd, Harwich, MA 02645

Property at 1424 Main St, Brewster, MA 02631, 3 beds, 1 bath

$749,000

3 beds1 bath3,021 sq ft

1424 Main St, Brewster, MA 02631

Property at 30 Grannys Ln, Orleans, MA 02653, 2 beds, 2 baths

$899,000

2 beds2 baths1,637 sq ft

30 Grannys Ln, Orleans, MA 02653

Property at 532 S Orleans Rd, Orleans, MA 02653, 3 beds, 3.5 baths

$889,000

3 beds3.5 baths2,937 sq ft

532 S Orleans Rd, Orleans, MA 02653

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than Redfin are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated Sat Oct 25 2025. Neither the listing broker nor Redfin shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. The Broker providing this data believes it to be correct but advises interested parties to confirm any item before relying on it in a purchase decision. All properties are subject to prior sale, changes, or withdrawal. © 2025 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

Pending Listings in South Brewster

There are currently 12 pending listings for sale in South Brewster at a median listing price of $998K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in South Brewster stay on the market for 62 days. Popular neighborhoods include South Orleans, East Orleans, Lower Cape, South Harwich, and Pleasant Lake. This map is refreshed with the newest listings in South Brewster every 15 minutes.

In the past month, 4 homes have been sold in South Brewster. Find your dream home in South Brewster using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in South Brewster are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in South Brewster. If you're looking to sell your home in the South Brewster area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in South Brewster with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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