56

Homes for Rent near Staples High School

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  • /39

    $8,500 per month

    • 4 Beds
    • 2.5 Baths
    • 2,478 Sq Ft
    • House for Rent

    16 Mortar Rock Rd, Westport, CT 06880

    Set at the end of a cul-de-sac in the desirable Compo South neighborhood, this lovely colonial home offers an ideal Westport location. Enjoy the view of the lush 0.57-acre lot from the charming screened-in porch. The perimeter is lined with spectacular mature perennials creating a private back yard oasis. Additional highlights include the trifecta of city water, city sewer, and natural gas.

    Agent Photo

    Linda Dunsmore

    Keller Williams Realty

    (475) 255-2935

    16 Mortar Rock Rd, Westport, CT 06880
  • /35

    $2,945 - $2,995 per month

    The Westporter

    1 - 2 Beds

    793 Post Rd E, Westport, CT 06880

    Welcome future Westporter resident! Your carefree modern lifestyle awaits. Elegantly designed and finished high-tech Smart-Townhomes offer the best of every world! These stylish condominium-level finishes boast quartz kitchen islands and upgraded stainless steel appliance packages. Plenty of natural light shines through floor-to-ceiling windows. State-of-the-art Smarthome technology includes full

    793 Post Rd E, Westport, CT 06880
  • /31

    $9,500 per month

    • 4 Beds
    • 2.5 Baths
    • 3,696 Sq Ft
    • House for Rent

    8 Peabody Ln, Westport, CT 06880

    Venture through stone pillars, nestled at the end of a private lane sits this beautiful 4-bedroom colonial harmoniously sited on a breath-taking, aw-inspiring parkland of cascading waterfalls, coi-pond for kayaking, zen gardens, botanicals & meandering stone paths. The large sun-drench rooms w/hardwood floors flow seamlessly from front-to-back living room w/gas fireplace, dining rm, large family

    Debbie Fisher William Raveis Real Estate

    8 Peabody Ln, Westport, CT 06880
  • /25

    $2,014 - $6,502 per month

    1177 Greens Farms

    Studio - 1 Bed

    1177 Post Rd E, Westport, CT 06880

    Suburban comfort mixed with urban convenience. Ideally located north of the Long Island Sound and one hour away from New York, our studio and one-bedroom homes are the perfect place to live and thrive. These Westport, CT, apartments are ready to satisfy all your needs through a wide range of amenities and services. Flexible lease terms are also available!Modern and airy our residences recreate

    1177 Post Rd E, Westport, CT 06880
  • /10

    $3,200 per month

    • 2 Beds
    • 1 Bath
    • 1,250 Sq Ft
    • House for Rent

    245 Main St, Westport, CT 06880

    Second floor apartment in downtown Westport location -walk to everything.

    Peter Hastings Hastings Real Estate

    245 Main St, Westport, CT 06880
  • /11

    $13,500 per month

    • 7 Beds
    • 7 Baths
    • 8,000 Sq Ft
    • House for Rent

    282 North Ave, Westport, CT 06880

    Property Id: 2122340Fabulous retreat from the city at a family compound like no other. Poised on 2.42 private acres, this Connecticut country home is beautifully renovated and surrounded exquisite landscaping. Relax on the covered front porch the terrace, gather with friends by the outdoor fireplace and roast smores by the firepit. A heated pool and spa, pool house, treehouse, zipline,

    282 North Ave, Westport, CT 06880
  • /6

    $7,000 per month

    • 4 Beds
    • 2.5 Baths
    • 2,084 Sq Ft
    • House for Rent

    5 Inwood Ln, Westport, CT 06880

    Located at the end of a serene cul de sac in the Compo Beach area of Westport. Just minutes to the Beach and Longshore Club. Owner prefers year-round rental, 12 month minimum. This home features a living room with vaulted ceiling, skylight and fireplace, and the dining room opens to a large deck. There are four nice sized bedrooms, Primary bedroom has its own bath. There is a large two car garage

    Charlotte Cotton William Raveis Real Estate

    5 Inwood Ln, Westport, CT 06880
  • /20

    $5,500 per month

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • House for Rent

    14 Long Lots Rd, Westport, CT 06880

    Call Flex terms unfurnished rental. Welcome to this beautifully renovated and charming cottage, a perfect rental nestled in the heart of town! Modern kitchen with newer cabinets, sleek appliances, hardwood flooring, and stunning quartz countertops. You'll love the spacious living room with custom built-ins and large sliding glass doors that fill the space with natural light all day long. Three

    14 Long Lots Rd, Westport, CT 06880
  • /22

    $5,450 per month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    66 Church Ln, Westport, CT 06880

    Fabulous Downtown Location! Fully REMODELED! New Kitchen, bath, windows, redone hardwood floors throughout, freshly painted !! Great apartment. Steps to town. In the heart of "Bedford Square". Natural light throughout the entire apartment. Very spacious rooms with hardwood floors. Lots of closet space. 2/3 bedrooms. 2 full baths, stacked washer/dryer. Master bedroom has a cool sitting area and 2

    Robin Singer Coldwell Banker Realty

    66 Church Ln, Westport, CT 06880
  • /12

    $7,400 per month

    • 3 Beds
    • 2 Baths
    • 1,583 Sq Ft
    • House for Rent

    2 Violet Ln, Westport, CT 06880

    Welcome to a sophisticated lifestyle in Westport! This contemporary home has been remodeled from top to bottom - new kitchen, new bathrooms, gleaming hardwood floors... An abundance of windows fills this home with cheerful sunlight while the level yard overlooks a scenic brook. Conveniently situated on a private lane, it's just across the street from restaurants, shopping, and a riverfront

    2 Violet Ln, Westport, CT 06880
  • /14

    $3,950 per month

    • 1 Bed
    • 1 Bath
    • 722 Sq Ft
    • House for Rent

    141 Main St Unit Upper floor, Westport, CT 06880

    Discover the perfect blend of comfort and convenience with this charming one-bedroom rental, ideally located in the heart of downtown Westport, CT. Just steps from the area's finest shops, restaurants, and cultural attractions, this apartment offers a vibrant urban lifestyle while providing a serene, private retreat. Spacious Living: Enjoy an open-concept living area with plenty of natural

    Matt Murray Higgins Group Bedford Square

    141 Main St Unit Upper floor, Westport, CT 06880
  • /11

    $4,600 per month

    • 3 Beds
    • 1 Bath
    • 1,604 Sq Ft
    • House for Rent

    10 Baker Ave, Westport, CT 06880

    Absolutely charming, and a stones throw from town. High ceilings, large 3 bedrooms, living room with stone fireplace, enclosed porch, dinning room off kitchen, plus one car detached garage in a great location. A great place to call home.

    Donna Karnes Century 21 AllPoints Realty

    10 Baker Ave, Westport, CT 06880
  • /34

    $9,500 per month

    • 4 Beds
    • 2 Baths
    • 2,284 Sq Ft
    • House for Rent

    9 Grays Farm Rd, Westport, CT 06880

    Flexible Long-term FURNISHED rental: $9500 yearly or $10500 short term FURNISHED. ALSO AVAILABLE UNFURNISHED SEE MLS#24126749. Fully remodeled, turn-key home on a premier estate property at the end of a cul-de-sac. Modern styling blends with a captivating private setting to create a unique oasis. Two acres of park-like property, abutting the Paul Newman-Poses Preserve, offer rare serenity in a

    Doug Bross Coldwell Banker Realty

    9 Grays Farm Rd, Westport, CT 06880
  • /34

    $8,750 per month

    • 4 Beds
    • 2 Baths
    • 2,284 Sq Ft
    • House for Rent

    9 Grays Farm Rd, Westport, CT 06880

    Flexible short-term UNFURNISHED rental: $8,750 yearly or $9,500 short-term. ALSO AVAILABLE FURNISHED SEE MLS# 24126753. Fully remodeled, turn-key home on a premier estate property at the end of a cul-de-sac. Modern styling blends with a captivating private setting to create a unique oasis. Two acres of park-like property, abutting the Paul Newman-Poses Preserve, offer rare serenity in a

    Doug Bross Coldwell Banker Realty

    9 Grays Farm Rd, Westport, CT 06880
  • /40

    $7,500 per month

    • 4 Beds
    • 3.5 Baths
    • 3,051 Sq Ft
    • House for Rent

    160 Hillspoint Rd, Westport, CT 06880

    Step back in time and experience the warmth of history at 160 Hillspoint Road, a Sherwood-built masterpiece dating back to 1790. This rare gem blends the timeless character of an antique home with the modern conveniences today's lifestyle demands. Perched high on the hill with sweeping views of Old Mill Beach and just a short stroll to Compo Beach, this residence offers an enviable coastal

    Nina Nyrop RE/MAX Right Choice

    160 Hillspoint Rd, Westport, CT 06880
  • /15

    $7,250 per month

    • 3 Beds
    • 3.5 Baths
    • 3,692 Sq Ft
    • House for Rent

    208 Bayberry Ln, Westport, CT 06880

    Discover the charm of this mid-century modern home, bathed in natural sunlight thanks to large windows that frame stunning views of the lush landscaping and nature outside. The updated kitchen boasts ample storage, including an updated laundry room/mudroom. The dining room features a wall of closets, perfect for storing linens and fine china. As you enter, you're welcomed by an open living room

    Georgia Wasserman Coldwell Banker Realty

    208 Bayberry Ln, Westport, CT 06880
  • /39

    $10,250 per month

    • 4 Beds
    • 3.5 Baths
    • 2,882 Sq Ft
    • House for Rent

    18 Bridge St, Westport, CT 06880

    Welcome to a Westport classic that blends the charm of circa 1884 with the comfort of today. Set on a level and professionally landscaped 0.82 acre property in Saugatuck, the home features high ceilings, detailed millwork, and wide plank hardwood floors. Sunlight fills the living and dining rooms, each with a fireplace, along with a cozy den and a bright home office. The island kitchen opens to

    Elizabeth Anrig Coach Lamp Living

    18 Bridge St, Westport, CT 06880
  • /40

    $49,900 per month

    • 4 Beds
    • 3.5 Baths
    • 1,692 Sq Ft
    • House for Rent

    19 Soundview Dr, Westport, CT 06880

    FABULOUS ON THE WATER SUMMER RENTAL~June, July and August. Price is monthly. Completely RENOVATED MOD CHiC !! Phenomenal WIDE WATER VIEWS. BIG covered front porch with outdoor fire pit in front yard and outdoor shower. Best Compo Beach views~Sunrise and Moonrise each day. Plenty of parking(6 cars, very rare) at this 4BD 2.2 Bath Compo Beach Bungalow. Come enjoy this incredible home with all the

    Robin Singer Coldwell Banker Realty

    19 Soundview Dr, Westport, CT 06880
  • /40

    $8,800 per month

    • 4 Beds
    • 3 Baths
    • 3,321 Sq Ft
    • House for Rent

    1 Brightfield Ln, Westport, CT 06880

    Fully Furnished Seasonal Rental in Westport - Fall 2025 through Spring 2026 Fully furnished contemporary home located on a quiet cul-de-sac, minutes from downtown Westport, beaches, and restaurants. Offering 4 bedrooms, 3 full bathrooms, and 4,711 sq ft of living space, this home features an open floor plan with high ceilings, oversized windows, and a double-sided brick fireplace. The property

    Alexey Gavrilov William Pitt Sotheby's Int'l

    1 Brightfield Ln, Westport, CT 06880
  • /33

    $8,000 per month

    • 2 Beds
    • 3.5 Baths
    • 2,774 Sq Ft
    • Townhouse for Rent

    504 Harvest Commons, Westport, CT 06880

    Enjoy everyday luxuries on a grand scale at Harvest Commons. This impeccably renovated townhouse offers accessible one level living and rarely found first & second floor suites. The main level includes a perfectly appointed gourmet kitchen. The open dining area has plenty of room for a 6-8 person table and has a lovely buffet/bar for entertaining. Both the kitchen and living rooms have sliding

    Carrie Perkins RE/MAX Heritage

    504 Harvest Commons, Westport, CT 06880
  • /26

    $7,500 per month

    • 3 Beds
    • 2 Baths
    • 1,348 Sq Ft
    • House for Rent

    45 Drumlin Rd, Westport, CT 06880

    Yearly unfurnished rental in a "walk to Compo Beach" neighborhood. This fully renovated home lives big with 3 bedrooms plus 2 full baths, a family room with fireplace, and an office/den w French doors to a private patio. The dining room, with built -in glass hutch, is large for entertaining or every day dining -right off the kitchen. The kitchen has granite surfaces and handsome stainless steel

    Sally Bohling Coldwell Banker Realty

    45 Drumlin Rd, Westport, CT 06880
  • /19

    $2,750 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • House for Rent

    1 Ridgewood Ln, Westport, CT 06880

    Charming one bedroom, one bath cottage yearly furnished rental in the Old Hill neighborhood of Westport. This stand alone cottage has lovely natural light with hardwood floors, high ceilings & a full kitchen with a breakfast bar. The primary bedroom has a walk in closet & hardwood floors. There is a stackable washer/dryer laundry in the full bath. The deck & additional patio offer lovely outdoor

    Mary Kate Klemish-Boehm Brown Harris Stevens

    1 Ridgewood Ln, Westport, CT 06880
  • /10

    $6,950 per month

    • 3 Beds
    • 2.5 Baths
    • 2,196 Sq Ft
    • House for Rent

    46 Old Rd, Westport, CT 06880

    Welcome to this charming colonial rental in Westport! Offering 2,500 sq. ft. with 3 bedrooms, 2.5 baths, a family room with fireplace, modern kitchen, laundry, and first-floor primary bedroom. Detached 2-car garage, attic, 0.50-acre lot, and recent interior & exterior updates complete this inviting home.

    Salvatore Dinardo Westfair Realty Group, LLC

    46 Old Rd, Westport, CT 06880
  • /31

    $3,400 per month

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft
    • House for Rent

    30 Crescent Park Rd, Westport, CT 06880

    Welcome to this beautifully remodeled two-bedroom, two-bath modular home located in a prime Westport community. Set within a modular home park, this property offers a excellent location just minutes to shopping, dining, and the train - ideal for commuters and anyone seeking convenience. Inviting open floor plan with luxury vinyl plank flooring, modern kitchen with stainless steel appliances, and

    Linda Almonte Berkshire Hathaway NE Prop.

    30 Crescent Park Rd, Westport, CT 06880
  • /21

    $3,200 per month

    • 2 Beds
    • 1 Bath
    • 1,286 Sq Ft
    • House for Rent

    148 Imperial Ave Unit 1, Westport, CT 06880

    Location location location! Winter Rental Furnished. This home is conveniently located in the very popular Imperial Avenue neighborhood. Centrally located between Westport Downtown and the Saugatuck area of restaurants and amenities. Walk to train, bike to the beach. This home includes formal Living Room (with fireplace), Family Room, Dining area, 2 Bedrooms (one currently set up as an office)

    Tree Roth Compass Connecticut, LLC

    148 Imperial Ave Unit 1, Westport, CT 06880
  • /15

    $4,900 per month

    • 3 Beds
    • 2.5 Baths
    • 2,996 Sq Ft
    • House for Rent

    145 North Ave, Westport, CT 06880

    An inviting yearly rental includes 3 bedrooms 2.5 baths, a deck overlooking an expansive yard for your use, highlighted with a gunite pool. This spotlessly ranch is ready for your enjoyment conveniently located in Westport, close to schools and town. Whole house generator. PLEASE NOTE THAT THE OWNERS WILL BE OCCUPYING THE APARTMENT (separate entrance) IN THE LOWER LEVEL ON A PART TIME BASIS.

    Lynne Nolan Compass Connecticut, LLC

    145 North Ave, Westport, CT 06880
  • /21

    $4,500 per month

    • 3 Beds
    • 1.5 Baths
    • 920 Sq Ft
    • House for Rent

    9 Crescent Park Rd, Westport, CT 06880

    Welcome home to this move-in ready 3-bedroom, 1.5-bath single-family in Westport, CT. Tucked in a prime commuter location, you're just minutes to the train, I-95, and the Merritt Parkway-with shops, dining, parks, and everyday amenities close by. Inside, a comfortable layout offers a bright living area, an eat-in flow, three well-proportioned bedrooms, and 1.5 baths. Enjoy easy living with a

    Karim Douich CT Asset Realty LLC

    9 Crescent Park Rd, Westport, CT 06880
  • /37

    $4,900 per month

    • 2 Beds
    • 1.5 Baths
    • 935 Sq Ft
    • Apartment for Rent

    201 Main St Unit 303, Westport, CT 06880

    Welcome to Belden Place! Discover Casual Luxury living personified in this boutique complex offering exquisite in-town living. This secure building with elevator access on the Saugatuck River is pet friendly. These luxury apartments are perfectly appointed and designed: plenty of closet space and storage, custom cabinetry, high-end appliances, in-unit washer and dryer, and private balconies.

    Sandra Calise Cenatiempo Settlers & Traders

    201 Main St Unit 303, Westport, CT 06880
  • /26

    $3,900 per month

    • 5 Beds
    • 3.5 Baths
    • 3,566 Sq Ft
    • House for Rent

    6 Summer Hill Rd, Westport, CT 06880

    Living is easy in this furnished Greens Farms neighborhood home. Furnished rental available Oct 15, 2025 to May 15, 2026. Contemporary ranch offers open, spacious rooms. Lovely fireplace in the ample living room. Large country kitchen opens to family room with fireplace and a wall of glass sliders. Formal dining area opens to an enclosed porch overlooking peaceful grounds. Tennis court on the

    Lynn Fraund William Pitt Sotheby's Int'l

    6 Summer Hill Rd, Westport, CT 06880
  • /40

    $20,000 per month

    • 6 Beds
    • 6 Baths
    • 7,500 Sq Ft
    • House for Rent

    35 Dogwood Ln, Westport, CT 06880

    Welcome to an extraordinary opportunity to lease a true architectural masterpiece. Tucked behind gates on a private street, this majestic 8,900 sq ft brick estate evokes the timeless elegance of a European castle while offering all the comforts of modern luxury. Set on 7.42 professionally landscaped acres, this one-of-a-kind residence features 6 generously sized bedrooms, 4 full baths, and 2

    Mark Sanford Berkshire Hathaway NE Prop.

    35 Dogwood Ln, Westport, CT 06880
  • /14

    $6,250 per month

    • 3 Beds
    • 2 Baths
    • 1,813 Sq Ft
    • House for Rent

    14 Northfield Dr, Westport, CT 06880

    Wonderful neighborhood, walking distance to Coleytown schools. 3 BR/2 Bath ranch with open floor plan and wonderful light filled family room. Interiors are scheduled to be freshly painted prior to new tenant occupancy. Tenant is responsible for all lawn and pool maintenance. Most recent tenant chose not to open pool for the last two seasons however pool was in working condition when last opened

    Deirdre Andreoli Compass Connecticut, LLC

    14 Northfield Dr, Westport, CT 06880
  • /21

    $7,500 per month

    • 4 Beds
    • 2.5 Baths
    • 1,542 Sq Ft
    • House for Rent

    18 Hales Rd, Westport, CT 06880

    XXXXX

    Scott Kelland CLS Group

    18 Hales Rd, Westport, CT 06880
  • /26

    $12,000 per month

    • 4 Beds
    • 3.5 Baths
    • 4,753 Sq Ft
    • House for Rent

    41 Burr Farms Rd, Westport, CT 06880

    Welcome to 41 Burt Farms Rd. Step into style and abundant space at this Westport home where contemporary flair meets exceptional value. Set at the end of a desirable street filled with extraordinary properties. The flexible layout of the home offers many possibilities for work from home and longer stay entertaining. Primary suite is set away from the other bedrooms offering privacy. The modern

    Meredith Cohen Serhant Connecticut, LLC

    41 Burr Farms Rd, Westport, CT 06880
  • /29

    $7,900 per month

    • 4 Beds
    • 3.5 Baths
    • 2,762 Sq Ft
    • House for Rent

    Unlisted Address

    High Point Road! Wonderful, spacious home on one of Westport's most popular cul de sacs! Spacious newer kitchen with granite and recently updated stainless steel appliances opens to vast stone patio overlooking private grounds. Huge living room with fireplace, formal dining room. 3 BRs up, including a primary suite with vaulted ceiling, private deck and ensuite updated bath. 4th bedroom suite

    Cyd Hamer William Pitt Sotheby's Int'l

    Unlisted Address
  • /13

    $13,000 per month

    • 5 Beds
    • 4 Baths
    • 4,835 Sq Ft
    • House for Rent

    99 Sturges Hwy, Westport, CT 06880

    Your very own vacation getaway. A gorgeous estate property, situated in the desirable Hunt Club/ Long lots area of Westport featuring a phenomenal and unique 5 bedroom, 4 bath Colonial Antique with a newly painted interior, an updated open floor plan, fabulous Interior and exterior entertaining spaces, gorgeous re-finished random wide-width hard wood flooring, Vaulted Ceilings, C/A, Gourmet

    Tanya Sprague William Raveis Real Estate

    99 Sturges Hwy, Westport, CT 06880
  • /25

    $12,500 per month

    • 5 Beds
    • 5.5 Baths
    • 7,995 Sq Ft
    • House for Rent

    37 Green Acre Ln, Westport, CT 06880

    Discover refined living in this 8,000 square-foot, 7-bedroom, 5.5-bath French Colonial residence, perfectly positioned as the last home on a quiet, dead-end private street. Combining timeless architecture with modern comforts, this estate offers exceptional privacy and a truly elevated lifestyle. Set on beautifully landscaped grounds, the home's stately exterior gives way to a thoughtfully

    Mark Sanford Berkshire Hathaway NE Prop.

    37 Green Acre Ln, Westport, CT 06880
  • /31

    $10,000 per month

    • 5 Beds
    • 4.5 Baths
    • 3,436 Sq Ft
    • House for Rent

    96 Kings Hwy N, Westport, CT 06880

    Historic Luxury Meets Modern Living in Old Hill, Westport Stroll to downtown Westport from this award-winning historic gem in coveted Old Hill. The David Judah House, c. 1760-honored with the 2016 Helen Muller Award for outstanding restoration-seamlessly blends timeless character with modern sophistication. Meticulously updated, the home features a chef's kitchen with Carrara marble countertops,

    Cyd Hamer William Pitt Sotheby's Int'l

    96 Kings Hwy N, Westport, CT 06880
  • /40

    $7,900 per month

    • 5 Beds
    • 4.5 Baths
    • 3,086 Sq Ft
    • House for Rent

    259 Wilton Rd, Westport, CT 06880

    Discover a spacious and flexible Westport ranch on nearly 2 private acres. The home features 5 bedrooms and 4 full baths. The main level includes 4 bedrooms, 3 baths, and an updated kitchen. The finished walkout lower level adds about 1,000 square feet and includes a separate apartment with a full kitchen, a bathroom, its own laundry, and a private entrance. There are three laundry areas in

    Inna Agujen Coldwell Banker Realty

    259 Wilton Rd, Westport, CT 06880
  • /18

    $2,975 per month

    • 3 Beds
    • 1 Bath
    • 1,373 Sq Ft
    • House for Rent

    36 Richmondville Ave, Westport, CT 06880

    Great in-town location, yet in a serene country setting. Large living Room with Fireplce and Hardwood floors. 3 bedrooms and a full bath. New interior paint.Mewer Kitchen and bath. Unit has 1-car garage, private washer and dryer. Convenient to Merritt PKWY, I-95, shops,Library, restaurants and cultural center. Please note that this unit is the first floor of a duplex (multi family) building.

    Ali Nabatchian RE/MAX Heritage

    36 Richmondville Ave, Westport, CT 06880
  • /39

    $6,500 per month

    • 3 Beds
    • 2 Baths
    • 1,212 Sq Ft
    • House for Rent

    9 Rowland Place, Westport, CT 06880

    Cloud 9 is a sweet pink cottage by the shore reminiscent of childhood days at the beach. Located at the end of a cul-de-sac four houses in from the water on Saugatuck Shores, this private home has an extra spacious, fully fenced, level yard giving you the best of both worlds - a lawn within a water community and quick access to the water. Home has three bedrooms and two baths on the main level.

    Pamela Wall Cool Cribs Real Estate

    9 Rowland Place, Westport, CT 06880

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